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Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 1: 307 - 318

DOI: https://doi.org/10.6023/cjoc202405027

ARTICLES

Copper(I)-Catalyzed Acylation/Cyclization of 2-Aryl-N-acryloyl Indole toward Indolo[2,1-α]isoquinoline Derivatives

  • Mengna Yang ,
  • Yucai Tang ,
  • Jie Jiang ,
  • Jiali Li ,
  • Ruohan Pan ,
  • Yu Chen ,
  • Jinglin Duan ,
  • Songbai Zhang
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  • Hunan Provincial Engineering Research Center of Electroplating Wastewater Reuse Technology, Hunan Provincial Key Laboratory of Water Treatment Functional Materials, College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, Hunan 415000
*E-mail:

Received date: 2024-05-21

  Revised date: 2024-06-26

  Online published: 2024-07-25

Supported by

Scientific Research Foundation of Hunan Provincial Education Department(23B0650); Scientific Research Foundation of Hunan Provincial Education Department(23A0503); Natural Science Foundation of Hunan Province(2022JJ30419); Innovation and Entrepreneurship Training Program for College Students(S202110549001S)

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Abstract

Indole[2,1-α]isoquinolines are an important class of bioactive molecules and show good antibacterial activity. In the present study, an efficient copper(I)-catalyzed acylation/cyclization has been developed for the construction of indolo[2,1- α]isoquinoline derivatives by utilizing 2-aryl-N-acryloyl indole and benzohydrazide as reactants in the presence of CuI as catalyst and tert-butyl hydroperoxide as oxidant. The present protocol exhibits good functional group tolerance, and a series of acylated indole[2,1-α]isoquinolines were synthesized in moderate to good yields. Radical trapping experiments indicated that the reaction may involve a radical process.

Key words： indolo[2,1-α]isoquinolin-6(5H)-ones; CuI; 2-aryl-N-acryloyl indoles; benzohydrazide; acylation/cyclization

Cite this article

Mengna Yang , Yucai Tang , Jie Jiang , Jiali Li , Ruohan Pan , Yu Chen , Jinglin Duan , Songbai Zhang . Copper(I)-Catalyzed Acylation/Cyclization of 2-Aryl-N-acryloyl Indole toward Indolo[2,1-α]isoquinoline Derivatives[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 307 -318 . DOI: 10.6023/cjoc202405027

References

[1]
(a) Singh, S.; Pathak, N.; Fatima, E.; Negi, A. S. Eur. J. Med. Chem. 2021, 226, 113839.
[1]
(b) Plazas, E.; Avila M, M. C.; Muñoz, D. R.; Cuca S, L. E. Pharmacol. Res. 2022, 177, 106126.
[1]
(d) Hostalkova, A.; Marikova, J.; Opletal, L.; Korabecny, J.; Hulcova, D.; Kunes, J.; Novakova, L.; Perez, D. I.; Jun, D.; Kucera, T.; Andrisano, V.; Siatka, T.; Cahlikova, L. J. Nat. Prod. 2019, 82, 239.
[1]
(e) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
[2]
(a) Tsyrenova, B.; Khrustalev, V.; Nenajdenko, V. J. Org. Chem. 2020, 85, 7024.
[2]
(b) Li, C.; Wang, Y.; Wu, S.; Zhuang, W.; Huang, Z.; Zhou, L.; Li, Y.; Chen, M.; You, J. Org. Lett. 2022, 24, 175.
[3]
(a) Mohan, C.; Krishna, R. B.; Sivanandan, S. T.; Ibnusaud, I. Eur. J. Org. Chem. 2021, 2021, 4911.
[3]
(b) Niu, Y.-N.; Xia, X.-F. Org. Biomol. Chem. 2022, 20, 7861.
[3]
(c) Zani, L.; Reginato, G.; Mordini, A.; Calamante, M. Synthesis 2016, 48, 3646.
[3]
(d) He, R.; Huang, Z.-T.; Zheng, Q.-Y.; Wang, C. Tetrahedron Lett. 2014, 55, 5705.
[4]
(a) Wang, C.; Sun, G.; Huang, H.-L.; Liu, J.; Tang, H.; Li, Y.; Hu, H.; He, S.; Gao, F. Chem. Asian J. 2021, 16, 2618.
[4]
(b) Shen, Z.-J.; Huang, B.; Ma, N.; Yao, L.; Yang, C.; Guo, L.; Xia, W. Adv. Synth. Catal. 2021, 363, 1944.
[4]
(c) Zhai, S.; Qiu, S.; Yang, S.; Hua, B.; Niu, Y.; Han, C.; Yu, Y.; Li, Y.; Zhai, H. Chin. Chem. Lett. 2022, 33, 276.
[4]
(d) Pan, Y.-L.; Gong, X.-M.; Hao, R.-R.; Zeng, S.-X.; Shen, Z.-R.; Huang, W.-H. RSC Adv. 2022, 12, 9763.
[4]
(e) Zhang, J.; Yang, Z.; Yu, J.-T.; Pan, C. Org. Biomol. Chem. 2022, 20, 3067.
[5]
Jiang, S.-S.; Xiao, Y.-T.; Wu, Y.-C.; Luo, S.-Z.; Song. R.-J.; Li, J.-H. Org. Biomol. Chem. 2020, 18, 4843.
[6]
Cui, H.; Niu, C.; Zhang, C. J. Org. Chem. 2021, 86, 15835.
[7]
(a) Yu, W.-Q.; Xiong, B.-Q.; Zhong, L.-J.; Liu, Y. Org. Biomol. Chem. 2022, 20, 9659.
[7]
(b) Zhang, D.-L.; Zhu, Z.-Q.; Xie, Z.-B.; Zhang, X.-P.; Le, Z.-G. New J. Chem. 2023, 47, 18354.
[8]
Zhao, P.; Wang, Y.; Wang, X.; Zhuang, D.; Yan, R. J. Org. Chem. 2022, 87, 9056.
[9]
Luo, Y.; Tian, T.; Nishihara, Y.; Lv, L.; Li, Z. Chem. Commun. 2021, 57, 9276.
[10]
Wei, Y.-L.; Chen, J.-Q.; Sun, B.; Xu, P.-F. Chem. Commun. 2019, 55, 5922.
[11]
Hu, X.-Y.; Xu, H.-F.; Chen, Q.; Pan, Y.-L.; Chen, J.-Z. Org. Biomol. Chem. 2021, 19,10376.
[12]
Zeng, F.-L.; Xie, K.-C.; Liu, Y.-T.; Wang, H.; Yin, P.-C.; Qu, L.-B.; Chen, X.-L.; Yu, B. Green Chem. 2022, 24, 1732.
[13]
(a) Li, A. F.; Ruan, Y. B.; Jiang, Q. Q.; He, W. B.; Jiang, Y. B. Chem.-Eur. J. 2010, 16, 5794.
[13]
(b) Pouliot, M. F.; Angers, L.; Hamel, J. D.; Paquin, J. F. Org. Biomol. Chem. 2012, 10, 988.
[13]
(c) Chauhan, J.; Ravva, M. K.; Sen, S. Org. Lett. 2019, 21, 6562.
[13]
(d) Yu, W.; Huang, G.; Zhang, Y. T.; Liu, H. X.; Dong, L. H.; Yu, X. J.; Li, Y. J.; Chang, J. B. J. Org. Chem. 2013, 78, 10337.
[13]
(e) Wang, L.; Wang, Y. Y; Chen, Q.; He, M. Y. Tetrahedron Lett. 2018, 59, 1489.
[13]
(f) Wang, Q.; Wang, X.; Liu, Q.; Xie, G.; Ding, S.; Wang, X. X; Fan, H. Org. Chem. Front. 2020, 7, 3912.
[13]
(g) Shu, W. M.; Zhang, X. Zhang, X. X.; Li, M.; Wang, A. J.; Wu, A. X. J. Org. Chem. 2019, 84, 14919.
[13]
(h) Wang, S.; Wang, K.; Kong, X.; Zhang, S.; Jiang, G.; Ji, F. Adv. Synth. Catal. 2019, 361, 3986.
[14]
(a) Takale, B. S., Telvekar, V. N. Chem. Lett. 2010, 39, 546.
[14]
(b) Pal, A., Das, K. M., Sau, S., Thakur, A. Chem. Asian J. 2023, 18, e202300755.
[15]
(a) Tang, Y.; Duan, J.; Yang, B.; He, Y.; Du, C.; Zhang, X. Org. Biomol. Chem. 2023, 21, 8152.
[15]
(b) Tang, Y.; Li, M.; Huang, H.; Wang, F.; Hu, X.; Zhang, X. Synlett 2021, 32, 1219.
[15]
(c) Tang, Y.; Dai, K.; Xiang, X.; Yang, Y.; Li, M. Org. Biomol. Chem. 2022, 20, 5704.
[16]
(a) Li, X.; Xu, X.; Zhou, C. Chem. Commun. 2012, 48, 12240.
[16]
(b) Xu, X.; Tang, Y.; Li, X.; Hong, G.; Fang, M.; Du, X. J. Org. Chem. 2014, 79, 446.
[16]
(c) Liu, S.; Zhao, C.; Pan, M.; Liao, H.; Liu, Y.; Zhang, J.; Rong, L. J. Org. Chem. 2023, 88, 16352.
[16]
(d) Chen, X.; Ouyang, W.-T.; Li, X.; He, W.-M. Chin. J. Org. Chem. 2023, 43, 4213 (in Chinese).
[16]
(陈祥, 欧阳文韬, 李潇, 何卫民, 有机化学, 2023, 43, 4213.)
[16]
(e) Gui, Q.-W.; Teng, F.; Yu, P.; Wu, Y.-F.; Nong, Z.-B.; Yang, L.-X.; Chen, X.; Yang, T.-B.; He, W.-M. Chin. J. Catal. 2023, 44, 111.
[16]
(f) Wang, K.; Huang, J.; Liu, W.; Wu, Z.; Yu, X.; Jiang, J.; He, W. Chin. J. Org. Chem. 2022, 42, 2527 (in Chinese).
[16]
(王苛莉, 黄静, 刘伟, 伍智林, 于贤勇, 蒋俊, 何卫民, 有机化学, 2022, 42, 2527.)
[16]
(g) Xie, L.-Y.; Peng, S.; Fan, T.-G.; Liu, Y.-F.; Sun, M.; Jiang, L.-L.; Wang, X.-X.; Cao, Z.; He, W.-M. Sci. China Chem. 2019, 62, 460.
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